4.7 Article

Flavylium based dual photochromism: addressing cis-trans isomerization and ring opening-closure by different light inputs

期刊

CHEMICAL COMMUNICATIONS
卷 51, 期 34, 页码 7349-7351

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc01677k

关键词

-

资金

  1. Fundacao para a Ciencia e Tecnologia [PEst-C/EQB/LA0006/2013]
  2. [SFRH/BPD/84805/2012]
  3. [SFRH/BPD/69210/2010]
  4. Fundação para a Ciência e a Tecnologia [SFRH/BPD/69210/2010] Funding Source: FCT

向作者/读者索取更多资源

The multistate system of 4',7-dihydroxy-3-methoxyflavylium is constituted by a multiequilibrium involving trans-chalcone, cis-chalcone, hemiketal, flavylium cation and quinoidal base. This system possesses two independently addressable inter-connected photochromic systems based on the cis-trans isomerization and ring opening-closure of the hemiketal.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Chemistry, Multidisciplinary

Natural and Synthetic Flavylium-Based Dyes: The Chemistry Behind the Color

Luis Cruz, Nuno Basilio, Nuno Mateus, Victor de Freitas, Fernando Pina

Summary: Flavylium compounds are a diverse family of plant pigments that contribute to a wide range of colors. There is growing interest in synthesizing different flavylium compounds with various substitution patterns for industrial applications. This Review provides an overview of the chemistry, synthetic and enzymatic approaches, and properties of flavylium-based compounds.

CHEMICAL REVIEWS (2022)

Article Chemistry, Applied

The Triumph of the blue in nature and in Anthropocene

Fernando Pina, Nuno Basilio, A. J. Parola, Maria J. Melo, Joana Oliveira, Victor de Freitas

Summary: Blue was the last color to be spread in Nature by anthocyanins, and the last color to be managed by Humans in Anthropocene. It took a long time for humanity to figure out how to reproduce and use blue, but plants developed strategies like intramolecular copigmentation and metalloanthocyanins to achieve the color. Blue was absent in early cave paintings and came later than red and green in LEDs and LASERs. It was only in the late 20th century that genetic engineering created blue flowers and blue remains sought after as a natural alternative to synthetic colorants. Despite being second-rate in the West, blue is now the preferred color in many countries.

DYES AND PIGMENTS (2023)

Article Biochemistry & Molecular Biology

The Use of Flavylium Salts as Dynamic Inhibitor Moieties for Human Cb5R

Oscar H. Martinez-Costa, Laura Rodrigues-Miranda, Sofia M. Clemente, Antonio Jorge Parola, Nuno Basilio, Alejandro K. Samhan-Arias

Summary: Cytochrome b(5) reductase (Cb5R) is a flavoprotein that participates in redox reactions and generates superoxide anion. Previous studies have shown that different flavonoids can inhibit Cb5R. This study aims to investigate the molecular mechanism of interaction between flavonoids and Cb5R using flavylium salts as dynamic inhibitors.

MOLECULES (2023)

Article Chemistry, Analytical

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

Liliana J. Gomes, Joao P. Carrilho, Pedro M. Pereira, Artur J. Moro

Summary: This study presents a new Near InfraRed (NIR) fluorescent chemosensor that can detect metal ions and anions. The sensor is based on a synthetic analogue of the natural anthocyanin family and has a metal chelating unit. It shows high sensitivity to Zn2+ and has selectivity towards ATP and ADP. The sensor also exhibits strong luminescence in bacterial and mammalian cells, suggesting potential applications in intracellular labeling.

SENSORS (2023)

Article Chemistry, Multidisciplinary

Parylene-Sealed Perovskite Nanocrystals Down-Shifting Layer for Luminescent Spectral Matching in Thin Film Photovoltaics

Ana Pinheiro, Andreia Ruivo, Joao Rocha, Marta Ferro, Joana Vaz Pinto, Jonas Deuermeier, Tiago Mateus, Ana Santa, Manuel J. J. Mendes, Rodrigo Martins, Sandra Gago, Cesar A. T. Laia, Hugo Aguas

Summary: The present study aims to enhance the performance of solar cells by developing advanced luminescent down-shifting using encapsulated nanostructured perovskite materials. Thin films of CsPbBr3 perovskite nanocrystal luminophores were synthesized and encapsulated with parylene type C to protect and stabilize the films. The results showed that this encapsulation technique significantly improved the current generation and spectral response of the photovoltaic cells.

NANOMATERIALS (2023)

Article Chemistry, Multidisciplinary

Photoswitchable Calixarene Activators for Controlled Peptide Transport across Lipid Membranes

Joana N. Martins, Beatriz Raimundo, Alicia Rioboo, Yeray Folgar-Camean, Javier Montenegro, Nuno Basilio

Summary: In this study, photoswitchable calixarenes were introduced to activate the transport of cationic peptide cargos across lipid membranes. The calixarenes, equipped with a hydrophobic azobenzene arm, can recognize cationic peptide sequences at the nanomolar range. The activation of membrane peptide transport was confirmed in synthetic vesicles and living cells by using calixarene activators with the azobenzene arm in the E configuration. This method allows the modulation of transmembrane transport of peptide cargos through the Z-E photoisomerization of functionalized calixarenes using 500 nm visible light.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Article Chemistry, Analytical

Colorimetric and Fluorescent Sensing of Copper Ions in Water through o-Phenylenediamine-Derived Carbon Dots

Roberto Pizzoferrato, Ramanand Bisauriya, Simonetta Antonaroli, Marcello Cabibbo, Artur J. Moro

Summary: Fluorescent nitrogen and sulfur co-doped carbon dots were synthesized through a simple one-step hydrothermal method and showed selective dual optical response to Cu(II) in water. The response was attributed to the formation of cuprammonium complexes or the oxidation of residual o-phenylenediamine bound to NSCDs. The NSCDs were successfully incorporated into a hydrogel agarose matrix for easier handling and sensing application.

SENSORS (2023)

Article Humanities, Multidisciplinary

A First Approach to the Study of Winsor & Newton's 19th-Century Manufacture of Madder Red Lake Pigments

Tiago Veiga, Artur J. Moro, Paula Nabais, Marcia Vilarigues, Vanessa Otero

Summary: This paper investigates the 19th-century manufacture of red lake pigments obtained from madder by Winsor & Newton (W&N). Three main synthesis methods were identified and reproduced, revealing three main steps. The pigments were characterized using various analytical techniques. The study aims to contribute new knowledge towards the identification and preservation of W&N's 19th-century madder colors in heritage objects.

HERITAGE (2023)

Article Polymer Science

Luminescence modulation of Tb/Eu@Polysulfone films for advanced anti-counterfeiting

Bernardo Monteiro, Joao Avo, Artur J. Moro, Claudia C. L. Pereira

Summary: In this study, emissive polysulfone thin films doped with tetracoordinated Tb3+ and Eu3+ complexes were successfully prepared. The emission of these films was regulated by simultaneous excitation light and heat, allowing for controllable emissive patterns. The addition of specific complexes promoted increased emission in the blue region, resulting in a dynamic irreversible generation of emissive color from green to cyan. Under a commercial 366 nm UV lamp, the selected pre-chosen pattern emitted brighter light in the blue region compared to non-irradiated films. A simple methodology was presented to prepare fingerprint emission profiles based on an unusual interaction between polysulfone, an aromatic polymer with intrinsic luminescence, and highly fluorinated lanthanide complexes for advanced anticounterfeiting technologies.

JOURNAL OF APPLIED POLYMER SCIENCE (2023)

Article Chemistry, Physical

Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery: From molecular design to the controlled release of doxorubicin

Dmitriy Moreira, Oren Regev, Nuno Basilio, Eduardo F. Marques

Summary: This study develops a delivery system based on dual light and pH responsive vesicles, which can achieve precise drug release. By adjusting the acid and base conditions and UV irradiation, the release of the drug is successfully controlled, demonstrating the potential application of vesicles as nano-carriers in acidic environments such as tumors.

JOURNAL OF COLLOID AND INTERFACE SCIENCE (2023)

Article Biochemistry & Molecular Biology

Lanthanide-Based Organic Salts: Synthesis, Characterization, and Cytotoxicity Studies

Andreia Forte, Sandra Gago, Celso Alves, Joana Silva, Joana Alves, Rui Pedrosa, Cesar A. T. Laia, Isabel M. Marrucho, Luis C. Branco

Summary: This study explores the formulation of magnetic ionic liquids (MILs) or organic salts based on lanthanides as anions. A set of choline-family-based salts, along with two other cation families, were combined with Gadolinium(III) and Terbium(III) anions. The magnetic moments of the lanthanides were found to be correlated with the structural features of the cation, and most of the prepared compounds were non-toxic to cells.

MOLECULES (2023)

Article Pharmacology & Pharmacy

In Vitro Antimicrobial Studies of Mesoporous Silica Nanoparticles Comprising Anionic Ciprofloxacin Ionic Liquids and Organic Salts

Luis Filipe, Telma de Sousa, Dario Silva, Miguel M. Santos, Manuela Ribeiro Carrott, Patricia Poeta, Luis C. Branco, Sandra Gago

Summary: The combination of active pharmaceutical ingredients in the form of ionic liquids or organic salts (API-OSILs) with mesoporous silica nanoparticles (MSNs) as drug carriers can enhance the capabilities of current antibiotics, especially against resistant strains of bacteria. In this study, three nanomaterials based on the modification of MSN surface with different ionic liquids coupled with anionic ciprofloxacin were prepared. These materials showed no cytotoxicity and exhibited improved antibacterial activity against both resistant and sensitive strains of K. pneumoniae. One particular nanomaterial, [MSN-Chol][Cip], showed significant enhancement with a tenfold decrease in MIC against sensitive strains. The importance of this study is rated at 8 out of 10 for its potential application in combating antibiotic resistance.

PHARMACEUTICS (2023)

Article Chemistry, Multidisciplinary

Phototransduction in a supramolecular cascade: a mimic for essential features of the vision process

Jialei Chen-Wu, Patricia Maximo, Patricia Remon, A. Jorge Parola, Nuno Basilio, Uwe Pischel

Summary: The tailored design of a light-triggered supramolecular cascade allows for the transduction of photons into chemical communication and the release of a neurotransmitter, reminiscent of crucial steps in natural vision process.

CHEMICAL COMMUNICATIONS (2023)

Article Chemistry, Physical

Modulating the thermodynamics, kinetics and photochemistry of 7-diethylamino-4′-dimethylaminoflavylium in water/ethanol, SDS and CTAB micelles

Paula Araujo, Joana Oliveira, Nuno Basilio, A. Jorge Parola, Victor de Freitas, Fernando Pina

Summary: The thermodynamics and kinetics of compound 7-diethylamino-4 '-dimethylaminoflavylium were studied in various solvents and in the presence of micelles. Different pH domains and photochemical reactions were observed in different solvents and micelles.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2022)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

Dan He, Yawen Li, Fuwen Zhao, Yuze Lin

Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.

CHEMICAL COMMUNICATIONS (2024)

Review Chemistry, Multidisciplinary

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

Olivier Monfort, Arshitha Madhusudhan, Martin Motola

Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Polymerization of monomer aggregates for tailoring and patterning water wettability

Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna

Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi

Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang

Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell

Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini

Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar

Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan

Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Wafer-scale synthesis of two-dimensional ultrathin films

Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal

Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi

Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.

CHEMICAL COMMUNICATIONS (2024)